


Starting a collection

by TheatricArcana



Category: Critical Role (Web Series)
Genre: BDSM, Blindfolds, Bondage, Dom Caleb RIGHTS babey!!!, Dom/sub, M/M, Multiple Orgasms, Painplay, Rough Sex, Sensory Deprivation, Strap-Ons, Trans Caleb Widogast, Trans Essek Thelyss, it's 3000+ words of trans shadowgast w caleb absolutely wrecking essek! What's not to love
Language: English
Status: Completed
Published: 2020-10-01
Updated: 2020-10-01
Packaged: 2021-03-07 19:53:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,341
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26743198
Author URL: https://archiveofourown.org/users/TheatricArcana/pseuds/TheatricArcana
Summary: Caleb gets a new toy to use on Essek, significantly larger than the one they had been using previously, but he doesn't tell Essek he bought a new one. Instead, Caleb blindfolds Essek and convinces Essek it's the same one they've been using previously, and Essek eats it up because he's a massive masochist.Check note at beginning for warnings!!
Relationships: Essek Thelyss/Caleb Widogast
Comments: 3
Kudos: 153





	Starting a collection

**Author's Note:**

> This isn't dubcon, they have safewords, Essek just doesn't use them because he doesn't want or need to. He's enjoying himself 100% of the time.
> 
> As far as warnings go, Caleb does kind of lie to Essek about what he's fucking Essek with? So perhaps that slightly blurs the line of consent? However if Essek was truly uncomfortable, he would have stopped Caleb. Besides that, I use the terms clit/breast/cunt to describe Essek's anatomy, there's brief mentions of Caleb experiencing dysphoria (though he's not really experiencing it while they're having sex), and I also mention Caleb having top surgery scars? That's about it as far as I can think of.
> 
> As always, I appreciate constructive criticism as long as you're gentle about it! Also any positive comments are appreciated LMAO

Caleb liked to think that he didn't spend coin on things that weren't truly worth it. He saw a good, logical reason to buy the things he bought for the most part, and this purchase had been no exception. The pleasure of Essek Thelyss was impossible to put a value on, and occasionally he spent a little more than he would like to admit in order to ensure that Essek would indeed be pleasured.

This purchase had maybe been a bit more for Caleb's pleasure than Essek's, however.

It was a very nice,  _ very  _ thick cock. Much bigger than the last one Caleb had been using, perhaps almost twice as large. Now that he was actually able to compare it to Essek's smaller frame in person, he wondered if perhaps his purchase had been a bit overambitious, but the desire to see Essek take it was close to overwhelming. Caleb had spent weeks fantasizing about getting it inside of Essek, anxiously awaiting being able to return to Xhorhas from his adventures so he could finally put it to use.

What was really doing it for Caleb right now though, was that Essek had  _ no  _ idea what was about to happen. Caleb hadn't even told Essek that he'd bought a new cock. In fact, Essek had blindly agreed without hesitation to try something new at Caleb's request. Caleb had never disappointed Essek in the past when he had allowed Caleb to surprise him before, so he saw no reason to deny Caleb this time.

Caleb carefully wove ropes around Essek's arms, tying perfect knots and avoiding any of the pressure points that could cut off blood flow with ease thanks to the help of his keen memory. The familiarity of the task had a calming effect for them both, and Caleb could see the tension start to bleed away from Essek as he relaxed into the comforting feeling of being bound by Caleb.

Caleb stood back for a second after he was done and admired his work. There was a gorgeous contrast between the soft hemp rope and Essek's beautiful dark skin that Caleb loved to look at. It was fascinating how good Essek looked tied up and helpless, considering the power he was capable of wielding in all other areas of his life.

"I need to blindfold you for what I have planned tonight. Is that okay?" Caleb asked softly, not wanting to disturb the room's currently calm atmosphere.

Essek simply nodded in response, leaning in towards Caleb to allow the blindfold to be slipped on easier, already looking a little blissed out. Caleb adored how easily Essek's submission came nowadays. It had been difficult to get Essek in the right headspace when they first started trying things like this, but once Essek realized how nice and relaxing it was to let Caleb take care of everything for a while, it became almost effortless to get Essek there.

And as odd as it felt to admit it, Caleb found himself craving the feeling of control he had during these moments between him and Essek. He had spent so much time in his life feeling helpless to the world around him, but despite it all he had perfect control of this, of  _ Essek-  _ who was completely at his mercy and perfect for Caleb to utterly wreck.

Caleb would get to that last part later, however.

Caleb found himself gently caressing Essek's face after adjusting the blindfold, and Essek nuzzled into Caleb's palm ever so slightly. Caleb wasn't even sure if Essek was consciously doing it, but it made a warm feeling spread inside his chest all the same, his heart still skipping a beat at the small intimacy even after all his time with Essek. It was a wonderful thing to see Essek without all those hardened edges from tension and stress.

Caleb couldn't help but indulge the both of them, leaning down to press Essek's softer lips to his own. Essek took a moment to react, of course, unable to even tell the kiss was coming, but he very quickly made up for it once he understood what was happening, parting his lips for Caleb instinctively.

Caleb pulled back first, a wet trail of saliva still attaching them for a second or two until Caleb shifted far enough away. Essek tried to chase after Caleb's lips, but without his vision to aid him and his arms tied behind his back, Caleb slipped out of reach easily.

Caleb didn't miss the little twitches of Essek's ears as he tried to track where Caleb was in the room with only his hearing. Caleb didn't explain what he was doing, either. He just let Essek continue to guess what was happening as he undressed and slid on the harness, silently as he possibly could with all the buckles attached to the ends of the soft leather straps that tended to clink together when not properly adjusted. Essek actually perked up a little at the telltale sound of the harness being adjusted, now understanding at least some of what Caleb had planned for the night.

Caleb rejoined Essek on the bed, sliding up to lean against the headboard and gently directing Essek to follow him. Caleb helped guide one of Essek's legs over him so Essek could straddle his lap, and Essek settled into Caleb's lap quickly, a content expression crossing his face at the familiar position.

A position that just so happened to put Essek's breasts directly in front of Caleb's face.

Caleb didn't quite have the same relationship with his body that Essek had with his own. Caleb still had faint scars across his chest, which were a reminder of one of the best decisions he had ever made in his own opinion. Caleb never once desired having breasts, therefore he was surprised to find out at first that Essek hadn't gotten rid of his, and even more surprised to find out that Essek genuinely preferred having them, but Caleb couldn't deny that they did look  _ very _ good on Essek. Caleb very quickly understood why Essek still liked having them. Every inch of Essek's lithe, gorgeous body belonged in a prestigious museum for fine art, and Essek's breasts were no exception.

Essek jumped ever so slightly when Caleb's hands came to rest on his waist, and then once again when he felt Caleb's hot tongue on one of his nipples with no warning. Caleb took his time there too, sucking and nipping at sensitive flesh before moving to the other side, no doubt leaving an outrageous amount of marks across Essek's breasts.

One of Caleb's hands slowly trailed between Essek's thighs, and Essek sighed in satisfaction when Caleb slid his fingers over Essek's sensitive folds, starting to rub his clit at a slow, lazy pace. Caleb didn't intend to rush, he could spend all night taking Essek apart with just his fingers, nipping and sucking Essek's nipples until they were raw and oversensitive, but Essek was significantly less patient. Only a handful of minutes had passed before Essek was rocking against Caleb's fingers, and Caleb indulged him when Essek requested more.

Caleb slid two fingers inside Essek, and Essek moaned softly at the subtle stretch. Caleb worked him open dutifully until he had three fingers sliding in and out of Essek with ease, grinding his palm against Essek's clit until Essek was shuddering and clenching around Caleb's fingers. It almost felt like Essek's cunt was trying to force Caleb's fingers out with how tight Essek got when he came, but Caleb resisted, keeping his fingers buried to the knuckle inside of Essek even when he shook and whimpered. Essek didn't know it yet, but he'd appreciate Caleb stretching him so thoroughly later.

Caleb let Essek catch his breath, stroking his waist comfortingly as he came down. When Caleb pulled his fingers out of Essek to reach for the oil, Essek groaned softly at the feeling of being empty again. Luckily, he wouldn't be empty for long.

"Do you want my cock?" Caleb asked, drizzling oil over said cock in order to prepare it for Essek.

Essek shivered before nodding enthusiastically. "I've been wanting it the entire time you've been gone."

Caleb couldn't resist a little grin. The thought of Essek wanting him and thinking about Caleb fucking him while he was gone was so, so lovely that Caleb couldn't help but press even more.

"Did you touch yourself thinking about this while I was gone? About me fucking you?" Caleb pulled Essek's hips down, so he could just barely rub the tip of the cock against Essek's soft folds, but he didn't let Essek go any further, waiting for Essek's reply first.

"I-" Essek turned a deep shade of purple, struggling to make himself admit it, but knowing he wouldn't get what he wanted if he didn't. "I did. Every time."

Caleb hummed approvingly as he relaxed his hold on Essek's hip, allowing him more room to move around. Caleb held the cock steady at the base, lining it up for Essek, knowing that Essek couldn't possibly do it himself with his arms still tied behind his back. Essek gasped a little at the first firm press of the cock against his entrance.

"Go at your own pace, I know it's been a few weeks since you've taken it." Caleb should have felt guilty for lying and telling Essek it was the same cock as before, but it only made it that much more exciting and mind numbingly arousing to watch. 

Essek eagerly tried to lower himself down, but very quickly his progress slowed, the head of the cock not even halfway inside of him before Essek's brow was furrowing, a soft noise of effort escaping him.

"Ah- it feels bigger than before?" Essek's voice was puzzled and slightly strained. Despite what seemed like discomfort, Essek was still trying to get more inside of him, just like Caleb knew he would.

Caleb could give up the charade now, tell Essek that it  _ was  _ actually bigger than before because it was an entirely different cock...

But there was no fun in that.

"It's only because it's been a while. Just take your time,  _ ja? _ "

Essek frowned but nodded, attempting to grind his hips down a little harder. Caleb could just barely see Essek make progress, the head slipping a few more centimeters inside before Essek's thighs started trembling with effort. It must have started to hurt at this point, but Essek chased after the pain with only the occasional whimper or soft groan of discomfort.

"I don't- I think it's too big." Despite the concerns he was voicing, Essek was still attempting to force more inside of himself. Gods, what Caleb wouldn't give to feel how tight Essek's cunt must be around that cock right now.

"It's nothing you haven't taken before, just relax."

Caleb was perhaps being a little mean, but he wasn't cruel. He placed the pad of his thumb against Essek's clit and worked it in slow circles, adding pleasure to the painful stretch. Essek made an absolutely ruined noise, but it seemed to help, as Essek began to redouble his efforts.

Essek drove his hips down particularly hard at one point, and Caleb could  _ feel  _ Essek almost convulse when the head finally,  _ finally  _ popped inside of his painfully tight entrance.

Essek's entire body jerked when it happened, his thighs quivering and a pained cry tearing out of his throat, followed by a series of almost panicked sounding gasps and whimpers that were concerning enough for Caleb to stop for a moment. Caleb knew from experience that Essek liked pain, but Essek's reaction was a little too intense for Caleb to not be worried. 

"Are you okay?" Caleb's tone was a little less calm than he would have preferred, the sudden anxiety hitting him that maybe this was a bad idea, but Essek nodded quickly, setting some of Caleb's fears to rest.

"I'm fine." Essek gasped out through gritted teeth. 

"Does it hurt?"

"Yes."

Caleb reached a hand up to cup Essek's cheek, pressing his thumb against Essek's lips. "Do you want more?"

" _ Yes. _ " Essek sobbed.

Essek cried out when Caleb thrust up into him, only a couple of inches, but it had Essek writhing in his bonds, legs shaking and on the verge of giving out.

The next thrust  _ actually _ had Essek's legs giving out. Essek made a strangled, wounded noise as he slid the rest of the way down onto the cock, taking it much faster than either of them meant for him to. Before Caleb could even ask if Essek was alright, Essek practically spasmed as his clit jumped and twitched under Caleb's thumb, his cries pitching several octaves higher, unmistakably orgasming in spite of, or maybe  _ because of  _ the pain.

The orgasm was almost punishing, even  _ more  _ pain being caused as a result of Essek's cunt clenching down on the cock like a vice grip involuntarily, so tight that Caleb wasn't even able to actually move it any further in or out of Essek as Essek rode out his climax. Essek sounded like he was being gutted alive, but every inquiry Caleb made as to if he was okay was met with enthusiastic nods, so Caleb made no effort to stop or pull out. 

Essek slumped boneless against Caleb after he was done, burying his face into the crook of Caleb's neck and staying there for a while. Caleb let him remain there for several minutes before breaking the silence.

"Are you done,  _ mein liebling _ ?"

Essek made a little noise of contemplation. "Not yet. Can I... have a few minutes first, though?"

"Of course you can." Caleb said, but then he thought for a moment before speaking up again. "Do you want me to untie you? You've been like this for quite a while now."

Essek hummed. "That would be nice."

Even though Essek's arms were behind his back, Caleb made quick work of the ropes, tossing it off the side of the bed, deciding to properly put it away later. 

Essek quickly used his newfound freedom of movement to snake his arms around Caleb's neck, sighing contently before they both fell back into comfortable silence for a while. The time was measured by their soft breathing and the quiet noise of Caleb's callused hands against Essek's soft skin as he soothingly slid his hands up and down Essek's back, comforting Essek as he took his breather.

It was so peaceful that Caleb honestly forgot that the cock was still buried to the hilt inside of Essek until Essek was rocking his hips down onto it again.

"I think I've still got one more in me." Essek said, as he attempted to raise his hips up again. However, his thighs shook with the effort and he barely raised himself up an inch before he was slipping back down again, unable to get his legs to cooperate with him. Essek laughed quietly. "Maybe I don't after all."

"Allow me." 

Caleb leaned forward, tilting Essek backwards until his back hit the mattress and he was sprawled across the bed underneath Caleb. Caleb took great care not to slide the cock entirely out of Essek as he repositioned them, but Essek gasped every time the movements jostled him and caused the cock to grind into him.

"How do you want it?" Caleb asked, rocking his hips into Essek, making him moan.

" _ Hard _ ."

Well, Caleb couldn't argue with a direction like that.

The first hard snap of his hips into Essek had Essek's nails clawing into his back, surely leaving angry red marks that would be visible later. From there, Caleb set a harsh, punishing pace, just like Essek has asked for.

Essek's lips found Caleb's again at some point, and Caleb happily swallowed the sounds of Essek's moans and cries of pleasure. After Essek had almost certainly drawn blood already, Caleb grabbed Essek's wrists and pulled Essek's nails away from the flesh of his back, lacing their fingers together before pinning Essek's hands against the bed, using the position to leverage himself as he fucked the cock in and out Essek. Essek voiced his approval loudly, with high pitched moans and half-formed words that he tried to slur out that sounded suspiciously like " _ Yes, more, harder _ ."

Essek came around the cock one last time, keening as he shuddered through his orgasm before falling back to the mattress, utterly exhausted in the wake of his third climax.

Caleb pulled away from Essek after he was sure Essek was done, and Essek hissed at the feeling of the cock sliding out of him for the first time in what felt like hours. Essek honestly couldn't tell whether or not he missed the feeling of it inside of him, but he felt  _ wrecked _ , his cunt aching pleasantly. He had never felt so thoroughly stretched open from Caleb's cock before.

Essek still hadn't taken off the blindfold, and he was too out of it to pay attention to the sound of Caleb removing the harness. However, Essek could tell Caleb had taken it off, as he couldn't feel it when Caleb settled back onto the mattress, unexpectedly grinding himself down against Essek's thigh.

Caleb was wet himself, wound up from watching Essek moan, writhe, and orgasm twice on the cock that Caleb had chosen just for him. It didn't take long for the arousal to build in his stomach, steadily working himself towards his own relief.

"I'm going to be honest-" Caleb began, a soft moan escaping his lips before he continued. "I lied."

Essek frowned. "About…?"

The blindfold was suddenly removed from Essek's eyes, and Essek struggled to adjust his vision for several seconds, even with the lights as dim as they were.

When he finally managed to focus, it was on the lovely view of Caleb working himself to completion against Essek's thigh, mouth slightly agape as he moaned Essek's name roughly. Essek could feel Caleb shuddering against his thigh when he tipped over the edge, and Essek let out a pleased hum before he slid his eyes to the side to see what Caleb was holding out in his hand and-

Oh _. Ohhh _ .

Essek understood now.

Not only was Caleb a liar, Caleb was a terrible, awful,  _ filthy  _ liar.

Essek laughed in surprise, looking at the cock he had never seen before, despite having just been fucked with it.

"That is very clever, but you are still the  _ worst  _ for it _. _ " Essek's tone was only teasing, and he couldn't even muster up the slightest attempts at a glare as he looked at Caleb, too sated for anything but a lazy smile.

"You enjoyed yourself then,  _ ja _ ?"

"Very much. If I'm being honest, I think I like this one much more than your old one."

"We'll keep both." Caleb mused. "Start a collection."

"A collection." Essek echoed, an amused tone in his voice at the thought. "Where did you even get it? I've never found anything in Rosohna like that."

"Nicodranas. Turns out there is a spectacular variety of items there. I would love to take you sometime- we could pick out some things together."

Essek chuckled. "Perhaps. I would need to disguise myself, though. I can't imagine the scandal it would cause if the Shadowhand was seen picking out sex toys with a human in a foreign country."

Caleb actually laughed himself. "It sounds bad when you put it like that."

Caleb moved to stand, beginning the process of properly putting everything away. Essek stretched out on the bed like a cat basking in the sun, making absolutely no effort to stand, making Caleb chuckle.

"I'd help, but I don't think my legs are going to work very well right now." Essek was only half joking, if he was being entirely honest.

" _ Nein _ , you earned your rest. I'll be back in just a moment."

By the time Caleb had cleaned the both of them up and put everything away, Essek was already theorizing about getting more fake cocks for their "collection".


End file.
